Unified synthesis of eudesmanolides,combining biomimetic strategies with homogeneous catalysis and free-radical chemistry |
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Authors: | Barrero Alejandro F Rosales Antonio Cuerva Juan M Oltra J Enrique |
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Institution: | Department of Organic Chemistry, Faculty of Sciences, Campus Fuentenueva s/n, University of Granada, E-18071 Granada, Spain. |
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Abstract: | reaction: see text] A general procedure for the synthesis of both 12,6- and 12,8-eudesmanolides has been developed. The key step is the titanocene-catalyzed radical cyclization of accessible epoxygermacrolides. The novel reagent 2,4,6-trimethyl-1-trimethylsilylpyridinium chloride, both compatible with oxiranes and capable of regenerating Cp(2)TiCl(2) from Cp(2)Ti(Cl)H and Cp(2)Ti(Cl)OAc, played an important role in the catalytic cycle leading to exocyclic alkenes. |
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